This dissertation consists of three essays on health inequalities that arise from interactions between education, gender, and socio-cultural context: gender disparities in the educational gradients in weight status, the gender-specific relationship between mortality of parents and offspring's educational attainment, and the association between adult literacy and self-rated health in 17 developed countries. Methodologically, I use multinomial regression, quantile regression, Cox proportional hazards models, and country fixed-effect approaches aligning my analytic strategies with the nature and scope of the research questions. The first chapter focuses on whether weight status is socially patterned by the interplay between human capital, economic, and behavioral resources in a highly gendered context of South Korea. The study shows that women who have fewer opportunities to transfer human capital into economic resources may utilize their human capital to obtain symbolic resources, such as physical attractiveness. In contrast, education is not a direct predictor of obesity among men, for whom behaviors promoting healthy weight often conflict with collective ideology at work such as heavy drinking and for whom motivation to obtain professional success is stronger than to obtain symbolic resources. The second essay focuses on intergenerational support from adult offspring to older parents and examines whether the relationship between children's educational attainment and parental mortality varies by the gender of the parent and the gender of the child. The study reveals that children's education is strongly associated with mothers' mortality beyond mothers' own socioeconomic status (SES). The relationship is less pronounced for fathers and is largely explained by the father’s own SES. Furthermore, sons' educational attainment is a stronger predictor of the mortality of parents than daughters' educational attainment. The third chapter examines whether literacy skills predict self-rated health beyond educational attainment in 17 developed countries using a cross-national survey, the Programme for the International Assessment of Adult Competencies (PIAAC). The study finds that the literacy-related health inequalities are less severe in countries with higher public share of health expenditures that may better address the needs of vulnerable individuals. Curriculum standardization also contributes to reducing health disparities by decreasing variance in skills obtained through education across individuals.